(2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one

Base Information

• Chemical Name: (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one
• CAS No.: 380621-63-6
• Molecular Formula: C₁₅H₁₃BrO₃
• Molecular Weight: 321.17
• Mol file: 380621-63-6.mol

Synonyms:(2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one

Chemical Property of (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one

There total 3 articles about (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

α-chloroacryloyl chloride (21369-76-6) + (2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole (380621-87-4) → (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one (380621-63-6)

Guidance literature:

Multistep reaction;

DOI:10.1039/b105376k

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one (380621-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 14.1 g / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 1 h / -20 - 10 °C

With (+)-camphor-10-sulfonic acid monohydrate; In dichloromethane;

DOI:10.1039/b105376k

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → (2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one (380621-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 14.1 g / (1S)-(+)-camphor-10-sulfonic acid monohydrate / CH₂Cl₂ / 1 h / -20 - 10 °C

With (+)-camphor-10-sulfonic acid monohydrate; In dichloromethane;

DOI:10.1039/b105376k

upstream raw materials:

α-chloroacryloyl chloride

(2S,3aS,7aS)-4-bromo-3a,7a-dihydro-2-phenyl-1,3-benzodioxole

benzaldehyde dimethyl acetal

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

Downstream raw materials:

(2S,3aS,4R,7R,7aS)-7-bromo-3a,4,7,7a-tetrahydro-2-phenyl-4,7-ethano-1,3-benzodioxol-8-one ethylene acetal

(1S,2S,3R,4R,5R,6E)-2-ethenyl-6-(2'-methoxyethoxymethoxymethylene)-3-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octane-2,5-diol

(1S,3E,4S,5S,6R)-5-ethenyl-5-hydroxy-3-(2'-methoxyethoxymethoxymethylene)-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one

(1S,4S,5S,6R)-5-ethenyl-5-hydroxy-6-[(4'-methoxyphenyl)methoxy]bicyclo[2.2.2]octan-2-one ethylene acetal